What's the most efficient way to deride a technology product as a stinker and/or a flop? Easy: Compare it to Microsoft Bob. Bring up the infamous Windows 3.1 front-end for computing newbies-officially released fifteen years ago this week, on March 31st, 1995-and you need say no more. Everything from OS X to Twitter to Google Wave to (inevitably) Windows Vista has gotten the treatment.

Bob's pervasiveness as an insult long ago transcended its brief period of prominence as a product. By now, it's unlikely that the vast majority of people who use it as shorthand for "embarrassing tech failure" ever actually used it-any more than the average person who cracks jokes about the Ford Edsel has spent time behind the wheel of one.

But Bob didn't start out as one of technology's most reliable laugh lines. It may strain credulity given Bob's current reputation, but back in 1995, even pundits who had their doubts about the software seemed to accept the idea that it was a sneak preview of where user interfaces were going. And even though Bob died just one year later, Microsoft continued to Bob-ize major applications for years -- most notably every version of Office from Office 97 through Office 2003, all of which featured the notorious Office Assistant helper, better known as Clippy.

In its own odd way, Bob is ripe for rediscovery. Hence our fifteenth-anniversary celebration, which includes the story you're reading; a guided tour of Bob in slideshow form; and memories of Bob and its offspring from Tandy Trower, who worked at Microsoft for 28 years. Whether you're appalled by Bob, defiantly enchanted by Bob, or never knew Bob at all, read on-and let us know what you think.

Bob was an outgrowth of a product that debuted in 1991 and lives on today: Microsoft Publisher. The well-reviewed desktop-publishing software was the first Microsoft application to simplify complicated tasks via Wizards that took users through complicated tasks step by step.

After finishing up Publisher, its designers, Karen Fries and Barry Linnett, pondered what to tackle next. Their minds remained focused on making software more approachable to newbies. Which was a logical goal: In 1995, the average American didn't even have a computer at home. (When Microsoft released Bob, it quoted projections saying that 46 percent of households would have a PC by 1997 -- and that was supposed to be a surprisingly high percentage.)

Fries and Linnett held focus groups and showed neophytes an interface with an animated waterfowl as an on-screen helper. In an interview with The Wall Street Journal, Fries remembered one man's response: "This guy was very emotional about it -- he grabbed my arm...He said, ‘Save all the money on the manuals and just give me this duck to always be there and tell me what to do.'"

The two then composed a provocative internal memo, arguing that Publisher was still too hard to use, and requested resources to develop a new interface for inexperienced users that would run on top of Windows. Bill Gates was intrigued. He gave the go-ahead for a project that was code-named Data Wizard at first, and then Utopia -- and which eventually shipped as Microsoft Bob.

Stanford professors and Bob influencers Clifford Nass and Byron ReevesMelinda French was named to head work on the product. A Microsoft employee since 1987, she became Bill Gates's fiancée in 1993 and his wife in 1994 -- facts which led many to conclude that Bob was a lousy idea which never would have gone anywhere if it wasn't for her involvement. But she was a Bob convert rather than its originator: Speaking of Fries and Linnett's work, she told the Wall Street Journal that "they were breaking the rules of things we'd done in software before -- I wanted to be a part of it."

And while the Journal reported that there were doubters inside Microsoft, others both inside and outside the company drank the Bob Kool-Aid early. As work on Utopia proceeded, two Stanford professors, Clifford Nass and Byron Reeves, signed on as consultants. Their research showing that people attribute human-like qualities to machines proved influential.

Reeves was later quoted in a Stanford news release:

The question for Microsoft was how to make a computing product easier to use and fun. Cliff and I gave a talk in December 1992 and said that they should make it social and natural. We said that people are good at having social relations -- talking with each other and interpreting cues such as facial expressions. They are also good at dealing with a natural environment such as the movement of objects and people in rooms, so if an interface can interact with the user to take advantage of these human talents, then you might not need a manual.

Nass and Reeves eventually joined Microsoft staffers on a press tour to promote Bob and the concept of "social interfaces" in general. "With a beta onscreen, these two academics summarized their research, which suggested that people found social interfaces helpful, friendly, and effective," remembers PCWorld Editorial Director Steve Fox, who was briefed during a previous PCW tour of duty. "The two editors in the room were trying not to snicker at the presentation."

Ultimately, the thinking that went into Bob-from Fries' talking-duck prototype to Nass and Reeves' university research-resulted in an integrated personal-productivity suite in which cartoon characters led users through apps that used images of a home as backdrop. The characters were called "personal guides," and included a dog named Rover (the default guide), a French cat, a rabbit, a turtle, a sullen rat, a gargoyle, William Shakespeare himself, and others. Each sat in the bottom right-hand corner of the screen, providing instructions in word-balloon form and performing bits of schtick as you used the software. (They spoke aloud, but only occasionally -- a sound card was a recommended accessory, but it wasn't mandatory.)

The package ended up with eight programs: a word processor, an e-mail program, a calendar, an address book, a checkbook writer, a personal finance info app, a household organizer, and a geography quiz. Microsoft envisioned that both it and third-party companies would release additional programs which could be installed within the Bob environment.

(For a full walkthrough of Bob -- from the word processor to the e-mail service to the estate planner (!) -- visit our guided tour.)

Fairly late in the game, the product apparently still didn't have a name: According to the Wall Street Journal, Microsoft considered monikers such as Home Foundation, Essential Home, and Portico before its ad agency, Wieden & Kennedy, suggested the name Bob in September of 1994. Microsoft later touted the name as being "familiar, approachable, and friendly," and acquired Bob.com from Boston-area techie Bob Antia so it could give users e-mail addresses at that domain. (After Microsoft Bob's demise, it eventually struck a deal with another guy named Bob to swap Bob.com for Windows2000.com.)

Bob was personified as a smiley face wearing Bill Gates-like spectacles, but even though the software that bore his name was rife with animated characters, he wasn't one of them. He appeared in the application itself only as a design element -- for instance, he was the tag on Rover's collar.

Karen Fries (left, in Bob T-shirt) and Melinda French look pleased by Bob's CES unveiling in this AP photo.On January 7th, 1995, Bill Gates strode onstage at the Consumer Electronics Show and revealed Bob to the world. He demoed the software and declared that it was a social interface, the first example of a new approach that would come to dominate computing. He even gave a sneak peek at a futuristic Son-of-Bob prototype from Microsoft Research: Peedy, a squawking 3D parrot who played Tears for Fears music in response to Gates's spoken request.

Multiple Hollywood potentates were seated in the front row: Steven Spielberg, David Geffen, Jeffrey Katzenberg, and Barry Diller. Some observers took their presence as a sign that Bob represented a new convergence of the software and entertainment industries. "They're seeing this kind of thing, the creativity here, and how we're actually drawing on sound companies and animators who come with a Hollywood background," Gates told the Associated Press.

Even if you were at CES but didn't attend Gates's speech, Bobmania was unavoidable. Flights heading into Vegas were supplied with Bob napkins, a plane towing a "Welcome Bob" banner circled above the Las Vegas Convention Center, and senior citizens wearing Bob sandwich boards trudged up and down the Strip.

In retrospect, the hoopla should have been taken with a humongous grain of salt: At later Vegas tech shows, Microsoft would hype such flops as Windows Smart Displays, Tablet PCs, and Smart Watches in similar fashion. Back in 1995, however, Microsoft-watchers responded to the Bob announcement respectfully. Even when they weren't wild about Bob itself, they took it seriously as a sign of where software was going.

At first glance all this twitching and prancing looks like a bizarre approach to interface design, but in fact the high-profile Bob characters have a purpose: They reinforce what Microsoft calls its new "social interface" between humans and PCs. In his CES keynote, Gates unveiled the intriguing new design principles behind Bob, principles that he predicts will become "the next major evolutionary step in interface design." In essence, Gates suggests that the next generation of high-powered PCs will abandon traditional graphical desktops in favor of "social" interaction with humanlike agents that can understand, learn, and interpret what the user wants. Initially, these agents will display only rudimentary intelligence and problem-solving abilities, but they'll quickly get smarter and more responsive as PCs acquire the necessary MIPS to run realistic simulations.

Many saw Bob as the next advance in software after the desktop-and-folders metaphor pioneered by Apple's Macintosh a decade before. A Microsoft Canada employee told the Toronto Star that a study showed that 84 percent of users with Macs at home preferred the Bob interface. Several newspaper stories published at the time make mysterious references to Apple having a Bob-like interface of its own in the works.

Analyst Charles Finnie of Volpe, Welty & Co. called Microsoft's product a threat to the very existence of Microsoft's competitor in Cupertino. "Bob is going to be another nail in Apple's coffin unless Apple can somehow raise the standard yet again on the ease-of-use front," he told the AP. That's as striking a piece of evidence as any that Bob wasn't immediately deemed a perverse joke back in 1995.

Bob Comes Home

Like many a Microsoft product before and since, Bob was announced before it was finished. The software didn't formally arrive in stores until March 31st, 1995, almost three months after its CES premiere. It sold for $99 -- a little on the pricey side, even though it was an era in which software generally sold for more than it would in years to come.

But Bob's pricetag wasn't as significant an issue as hardware requirements. The program demanded a PC with a 486 CPU, 30MB of free disk space, and what the Puget Sound Business Journal called "a huge amount of memory" -- 8MB, or twice the typical amount that circa-1995 home PCs sported. Newbies would only be able to experience Bob if they owned unusually potent computers.